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Search results; Over 1,000 homes in Pine Plains

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Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
3 bedrooms, 3 beds, 2 private bathrooms
3–8 Oct
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5.0 out of 5 average rating, 61 reviews
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Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
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Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 280 reviews
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Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 169 reviews
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Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
4.96 out of 5 average rating, 23 reviews
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Guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds, 4.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 24 reviews
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Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
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Guest favourite
Home in Pine Plains
Silo-country home steeped with delicious touches.
5 bedrooms, 9 beds, 2.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Pine Plains
Hudson Valley Retreat: Pool, Views, Chef's Kitchen
5 bedrooms, 6 beds, 5.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Pine Plains
Stony Hill Haus in Pine Plains
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.97 out of 5 average rating, 110 reviews
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Superhost
Room in Pine Plains
The Smithfield Room
1 bed, 1 bathroom
4–9 Oct
4.75 out of 5 average rating, 12 reviews
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Guest favourite
Cabin in Red Hook
Design-Forward Riverfront Cabin on 120 Acres
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 136 reviews
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Top guest favourite
Home in Red Hook
Taconic Hill-a modern retreat on 50 forested acres
4 bedrooms, 6 beds, 3 bathrooms
10–15 Sept
4.95 out of 5 average rating, 41 reviews
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Home in Millerton
The House in a Beautiful Small Upstate Town
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 263 reviews
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Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
2 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 748 reviews
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Guest favourite
Home in Craryville
Lakeside Lodge • Firepit • Lake access • Sleeps 10
5 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 63 reviews